Oakland Vacations from $586
Book a Hotel + Flight or Car together to unlock savings
Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
Downtown Pittsburgh
Save 100% on your flight
Price was $869, price is now $586 per person
$586
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (313 reviews)
Very responsive, great location, awesome hosts! 10/10 would recommend.
Reviewed on Jul 31, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was $1,008, price is now $758 per person
$758
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,583 reviews)
The room was very clean and the bed was very comfortable
Reviewed on Aug 4, 2026
EVEN Hotel Pittsburgh Downtown by IHG
Downtown Pittsburgh
Price was $967, price is now $730 per person
$730
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.8/10 Excellent! (1,102 reviews)
Ice machine was not working on our fifth floor room; fortunately, merely a few extra minutes on elevator to floor six for ice.
Reviewed on Jul 30, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was $1,260, price is now $964 per person
$964
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
The staff at the Westin was extremely helpful and proactive. The initial room they gave us had some issues, including a smoke-like smell (not cigarette smoke). As soon as we notified reception, someone handled it extremely professionally, and within minutes we were moved to a much better room.
Reviewed on Aug 3, 2026
The Maverick by Kasa
East Liberty
Price was $1,175, price is now $908 per person
$908
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9/10 Wonderful! (1,011 reviews)
There is no staff, only an AI chatbot that is not helpful and will stop responding to your questions/messages after a few minutes
Reviewed on Aug 3, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
$119 nightly
The price is $136 total per night from Aug 31 to Sep 1
$136 total
Aug 31 - Sep 1
Total with taxes and fees
9/10 Wonderful! (846 reviews)
"Very comfortable"
Reviewed on Aug 3, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $130 total per night from Aug 9 to Aug 10
$130 total
Aug 9 - Aug 10
Total with taxes and fees
Residence Inn Pittsburgh Oakland/University Place
3341 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from Aug 9 to Aug 10
$148 total
Aug 9 - Aug 10
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
"Wifi issues making connection very challenging. Also, pool needs updating (more water need in pool, better lighting, dingy ceiling, too heavily chlorinated). Better gluten free breakfast options needed too. Thanks!"
Reviewed on Jul 31, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Oakland attractions
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
$48
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
90% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
$33
per adult
Explore a world of travel with Expedia
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- Visit Downtown Pittsburgh
- Schenley Park
- Carnegie Museum of Art
- Strip District Vacations
- Cathedral of Learning
- Pittsburgh Vacations
- Carnegie Mellon University
- North Shore Vacations
- National Aviary
- Acrisure Stadium
- Carnegie Library of Pittsburgh
- Byham Theater
- Carnegie Science Center
- Grandview Overlook
- Andy Warhol Bridge
- Children's Museum of Pittsburgh
- Monongahela Incline
- Senator John Heinz Regional History Centre
- Lighthouse ArtSpace Pittsburgh
- Visit Pittsburgh
- Duquesne Incline
- University of Pittsburgh
- Phipps Conservatory
- Ppg Paints Arena
- Kennywood
- Where to stay in Pittsburgh
- Roberto Clemente Bridge
- Andy Warhol Museum
- Petersen Events Center
- Point State Park
- The Nationality Rooms
- David L Lawrence Convention Center
- U.s. Steel Tower
- Heinz Memorial Chapel
- Soldiers and Sailors Memorial Hall and Museum
- Market Square
- Pnc Park
- Photo Antiquities Museum of Photographic History
- Carnegie Museum of Natural History
- Rachel Carson Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.